192937-16-9

Upstream product

• 625-59-2 2-propyl thiocyanate 
• 100-01-6 4-nitro-aniline 
• 75-31-0 isopropylamine 
• 2131-61-5 p-nitrophenyl isothiocyanate 

Downstream Products

• 859785-61-8 N'-isopropyl-N'''-(2-methoxy-phenyl)-N,N''-p-phenylene-bis-thiourea 
• 859785-63-0 N'-isopropyl-N'''-(4-methoxy-phenyl)-N,N''-p-phenylene-bis-thiourea 
• 859736-57-5 N'-isopropyl-N,N''-p-phenylene-bis-thiourea 
• 16349-62-5 3,3'-diisopropyl-1,1'-p-phenylene-bis-thiourea 
• 457939-57-0 N-(4-amino-phenyl)-N'-isopropyl-thiourea 

Relevant academic research and scientific papers

Iprodione degradation by isolated soil microorganisms

Three bacterial strains were isolated from soils adapted to iprodione and identified as Pseudomonas fluorescens, Pseudomonas sp. and Pseudomonas paucimobilis. The first two strains transformed iprodione to N-(3,5- dichlorophenyl)-2,4-dioxoimidazo-lidine (II) and under restrictive conditions to 3,5-dichlorophenylurea acetic acid (III); the latter subsequently degraded II to III and III to 3,5-dichloroaniline (3,5-D). We constructed bacterial combinations consisting of Pseudomonas paucimobilis plus one of the iprodione degraders and showed that these combinations transformed iprodione into 3,5- D. It is known that 3,5-D was the major metabolite found in adapted soils, suggesting that such a bacterial combination might be responsible for degrading iprodione into 3,5-D in adapted soils. Plasmids could only be isolated in Pseudomonas fluorescens but we did not investigate if one of these was involved in the ability to degrade iprodione.

Ph3P/I2-mediated synthesis of N,N′,N″-substituted guanidines and 2-iminoimidazolin-4-ones from aryl isothiocyanates

A convenient one-pot procedure for the synthesis of acyclic and cyclic guanidines mediated by the Ph3P/I2 system is described. Sequential condensation of aryl isothiocyanates with amines followed by dehydrosulfurization and guanylation could lead to both symmetric and unsymmetric N,N′,N″-substituted derivatives. Through a tandem guanylation-cyclization, a series of 2-iminoimidazolin-4-ones could also be prepared in good yields from the reaction of aryl isothiocyanates with amino acid methyl esters.

A model for a solvent-free synthetic organic research laboratory: Click-mechanosynthesis and structural characterization of thioureas without bulk solvents

The mechanochemical click coupling of isothiocyanates and amines has been used as a model reaction to demonstrate that the concept of a solvent-free research laboratory, which eliminates the use of bulk solvents for either chemical synthesis or structural characterization, is applicable to the synthesis of small organic molecules. Whereas the click coupling is achieved in high yields by simple manual grinding of reactants, the use of an electrical, digitally controllable laboratory mill provides a rapid, quantitative and general route to symmetrical and non-symmetrical aromatic or aromatic-aliphatic thioureas. The enhanced efficiency of electrical ball milling techniques, neat grinding or liquid-assisted grinding, over manual mortar-and-pestle synthesis is demonstrated in the synthesis of 49 different thiourea derivatives. Comparison of powder X-ray diffraction data of mechanochemical products with structural information found in the Cambridge Structural Database (CSD), or obtained herein through single crystal X-ray diffraction, indicates that the mechanochemically obtained thiourea derivatives are pure in a chemical sense, but can also demonstrate purity in a supramolecular sense, i.e. in all structurally explored cases the product consisted of a single polymorph. As an extension of our previous work on solvent-free synthesis of coordination polymers, it is now demonstrated that such polymorphic and chemical purity of selected thiourea derivatives, the latter being evidenced through quantitative reaction yields, can enable the direct solvent-free structural characterization of mechanochemical products through powder X-ray diffraction aided by solid-state NMR spectroscopy.